First Time's the Charm
by LadyClassical
Summary: Regulus survived the Drink of Despair, and by the 1990's he is a successful businessman, the owner of a chain of popular deep-dish pizzerias. He is also dating sexy, curvaceous Holly Greengrass, a grown-up cousin of Daphne and Astoria. He wants to remain chaste until marriage, but will all that change with one late-night booty call? (Innocent!Regulus, RABxOC, rated M for smut)


Regulus Black normally stayed late at work. When he was at the corporate office, he could hope to be home by seven. But when he was at the restaurant, he often didn't get home until midnight. Being a small business owner was a lot of work, but it was rewarding. Being an ambitious, opportunistic Slytherin paid off in the business world, he'd found.

Now that Harry was staying with him at #12 Grimmauld Place, though, Regulus tried to get home by six or seven every day, so they all could have dinner together. It was ten to six right now, and he was just thinking about it when the phone rang.

"Reggie's Pizza Empire, this is Reggie Black speaking, how may I help you?" he said politely.

"Hi," said a familiar, bright voice on the other end.

"Holly?" Regulus was surprised, but only mildly. He never said his girlfriend, Holly Greengrass, _couldn't_ call him at work, but he didn't expect her to.

"Yep, it's me," she said. "Listen…do you want to come and visit me in Hogsmeade this evening? At my apartment?"

"I'd love to, Holly, but remember, I have to go home to eat dinner," Regulus reminded her. "Kreacher misses me during the day, and he likes sitting at the table with me."

"Oh…" Holly paused. "Well, it won't take long. I just have something to ask you."

"Very well, then," Regulus told her. "I'm just leaving work now. I've got someone to cover the store until closing tonight."

Regulus then Apparated into Hogsmeade, right outside of the Three Broomsticks; Holly lived in an apartment on top. He looked over at the High Street, where they were building the newest Reggie's Pizza Empire. Hopefully he'd manage to find waitstaff, bussers, chefs, a store manager, an operations manager and all other kinds of things before it was set to open in June. It was all very stressful.

There was no elevator up to the apartments, just stairs, but Regulus didn't mind walking. When he got there, he used the _Orchideous_ spell to cast her some roses, and knocked.

"Hey there, Reggie," said Holly, opening the door. She was wearing very tight jeans and a loose white button-down shirt. He couldn't help wondering if she was wearing a bra or not, because her big breasts kind of sagged a little.

"Hello." Regulus handed her the flowers, wondering why in the world she called him that. Reggie was only his name in the business world, or when Sirius was making fun of him, which was often. "Anyway, Holly…why did you want to see me?"

"Well," Holly began, looking like she was choosing her words very wisely, "I'd like to talk about the…the _physical_ aspect of our relationship."

"The physical aspect?"

"Yeah," she said. "You know, we haven't had sex yet. In fact, we haven't gotten beyond first base."

Regulus was shocked she'd be so…so _forward_. After all, last year she had done so much complaining about how men never thought of her as more than a sex object. So he had made sure to keep his eyes on her face, always. Now what was she saying?

"And you're still a virgin, aren't you?" she continued.

"How did you know that?" said Regulus sharply.

"Lucky guess." Holly shrugged. "But anyway, I just wanted to know if you were against it."

"It's not so much that I'm against it, it's just that…" Regulus frowned. "Well, I wanted to be a virgin on my wedding night."

This didn't have the reaction he'd expected, which was surprise. Holly didn't look surprised at all, in fact. She just shrugged again.

"I can respect that," she told him, but she looked a little glum as she said it.

"May I—may I sit down?" Regulus asked uncomfortably. She nodded and led him to her threadbare couch. Regulus knew Holly was working in the Three Broomsticks in exchange for a small flat on top of the building. Since her salary was her living quarters, Regulus could only assume she paid for things like this with all the money she got from tips—and, after all, with looks like hers, tips were probably easy to come by.

When she leaned into him, Regulus realized Holly definitely wasn't wearing a bra. The shirt was a thin, breezy type of material, and as she snuggled into him, he could feel her nipples pressing into his side. She just closed her eyes and smiled, letting them hang freely; they felt like soft, squishy pillows, except for the nipples, which were hardening. Regulus could suddenly feel a familiar tightening sensation around his crotch area.

Oh _no_. With all his efforts to be a gentleman, with all his determination to save his virginity for his wedding night, his body had given him away. Regulus crossed his legs, hoping Holly hadn't noticed. It was typically possible to discreetly slip an ice cube down there to fix things, which he had done at more work parties and hosting events than he'd care to admit, but she hadn't actually offered him a drink.

"Come on, Reggie," she whispered suddenly into his ear. "I know you want to stay a virgin, but we can at least make out, can't we?"

Regulus tried to picture something that would get rid of his erection—like Cornelius Fudge wearing nothing but a lime-green thong, which was what Sirius said he utilized. But even that didn't work, because the image, however disturbing, was overpowered by images of Holly wearing no clothing at all.

"Oh…well, I don't know," said Regulus, fiddling with his tie. "Maybe."

"Just a little kiss, Reggie," Holly said seductively, kneeling on the sofa and turning Regulus to face her. "Maybe…just maybe…"

Regulus was undeniably horny. Perhaps he wanted to be a virgin on his wedding night, but it couldn't hurt to make out a little. Regulus wasn't so experienced in that, but suddenly it didn't matter. He grabbed Holly by the shoulders and pressed his lips against hers, the electric feeling spreading throughout his body and all the way down to his penis, which by now wanted her so badly…but he _couldn't_.

Holly's tongue was pressing against Regulus's teeth. It was a French kiss! Even though he had never done that, he knew what it was, so he parted his teeth and kissed her with his tongue, too. He found that it came rather naturally to him (although, of course, most things did). And as they kissed, they slowly sank down on the couch, Regulus on top of Holly as she leaned her head on the armrest of the couch…Regulus kissed her with his mouth open and his eyes shut, and perhaps his eyes being shut gave him courage, for that was when he moved his wand hand downwards.

If she said no, of course, he would stop it, but she didn't say no. In fact, she seemed to be encouraging it; she put her hand on top of his and squeezed it for a split second. By now, he was on top of her, so he was sure she felt his boner, but he found he didn't care. Her breasts were warm and soft, and his fingers wandered to one of her nipples, which he played with for a little while. She moaned with satisfaction, which turned him on even more; his blood, most of which was in his penis now, was boiling with passion for her.

Regulus kept kissing Holly as he slipped one hand into her shirt. The skin on her breasts was so smooth…It was a heavenly feeling, touching these special parts of her, just the fact that he _got_ to touch them. So he unbuttoned her shirt, all the way down, leaving her wearing absolutely nothing from the waist up.

When that was done, Regulus stopped kissing her for a minute and looked deep into her olive-green eyes, at her shoulder-length brown hair, at her whole curvy body, big, beautiful breasts and hips but a smaller waist. He ran his fingers up and down the natural hills and valleys of her sides, making her shiver. When she went braless, he saw that they were not round but more teardrop-shaped, one falling slightly to the left, the other to the right. The nipples were pink and erect; his fingers played with one while he put the other in his mouth, not so much sucking but rather licking it like a lollipop, loving the way she squirmed with pleasure and couldn't seem to control her yelps. Once he was finished, she sat up, her eyes overbright.

"Oh, Reggie, I was full of sexual pleasure," she gasped. Then, to his shock, she lowered her hand and set it on his crotch. "But I don't want it all to be about me…"

Regulus sucked in his breath and just watched in shock as she unbuckled his belt for him and unzipped his pants; he couldn't help noticing that whenever she moved, her breasts, no longer confined by a bra, kind of swung along with her. When she pulled down his underwear he felt his private parts hit the cold air, but this time he was the one groaning in pleasure, because now they finally felt free. He felt a little self-conscious at first, since this was the first time she'd seen this part of him—in fact, unless you counted his mother, this was the first time _any_ woman had seen this part of him. And now that he was exposed, his erection was a lot more noticeable.

"Hmm," said Holly. "Did I order an extra-large sausage?"

"Well, we do deliver," Regulus told her anxiously. He was hyperventilating and a little shaky, anticipating whatever she was going to do to him. The last thing he was thinking about right now was work.

"I haven't got any money for pizza, Reggie, but maybe we can work something out." Holly licked her lips, leaned right down and kissed his penis just once, quickly, and then drew away. It was positively tantalizing; her lips were warm, soft and wet, and he just wanted more.

Holly slowly tugged Regulus's pants and underwear all the way down to his knees and pushed his legs apart, then got on her hands and knees while he continued to lay flat on his back. It felt like she was acting sexually dominant now, and that was so incredibly hot…With a sort of wild look in her green eyes she grabbed his hands and pinned them back, then leaned in to kiss his lips again…Once more her breasts brushed up against his body, and he could feel the build-up down there, pressing on his nerves. As they kissed she worked on the green-and-silver tie around his neck, and when she had it off of him, she held it in her wand hand like a whip. She looked down at him with an almost wicked grin.

"Come on, Reggie, you gotta beg for it," she crooned, wrapping his tie around his wrists. She held it there with one hand, and with her other, she slowly stroked his penis with her index finger, starting at the bottom and going all the up way to the tip. "You want it?"

"I want it," he moaned.

"What do you want?" she demanded.

" _You_ ," he told her almost painfully, and he heard her laugh. She moved her body back until her mouth was level with his crotch; he knew what she was going to do, of course, as he felt his feet and hands tense up, but there was no way he could ever have prepared for it. He didn't know what it was about tongues, but from the moment he felt her hot breath on the tip of his penis, then her soft wet lips tightening onto him, it felt completely amazing, even more so when she wrapped her tongue around him, sliding it back and forth along the shaft. Finally, she stuck the whole thing in her mouth, going all the way down and deep-throating. She took it out of her mouth and licked it again, from the bottom to the tip, grinning up at him. It was hot even to _watch_ her, and the sensation was driving him insane.

Down she moved until she got to the testicles…sucking on _those_ …That felt the best of all. It was uncontrollable; Regulus just let his cries of pleasure out, especially since they seemed to encourage her. Barely knowing he was doing it, he grabbed her hair and pulled her head forwards a little, reveling in the feeling of her tongue and lips; he just needed something to grab onto, an outlet for this stimulation while she blew not just his testicles but his mind as well. Somewhere far away, he heard another muffled laugh. She was getting smug satisfaction from having such control over him. Why was he so turned on by that?

Holly didn't let Regulus ejaculate…not yet, at least. As she pulled her mouth off his testicles, he was just left gasping for breath, trying not to pass out, as she unbuttoned his shirt and pressed into him, rubbing her smooth skin, especially her breasts, against his body. It was really the wetness and the tightness he'd loved about the oral, but if that was how it felt when his penis went inside her mouth, how on Earth would it feel when it went inside her vagina? And he asked himself, as her hair brushed against his cheek, why was he waiting until marriage? Holly wasn't some random floozy he'd picked up in a bar. She was a talented witch from a respectable pureblood family, they'd been dating for some time now, and he loved her. Not only that, but if they didn't have sex now, chances are he would be finishing this himself at home, and that wouldn't be nearly as fun.

"You want my lips down there again, Regulus?" she hissed into his ear.

"Yes!" he said, completely honestly.

"Which ones?"

Just a little of the blood from poor Regulus's erection came creeping back up into his face, but she was going to make him say it, he knew, so he said, "The ones…down there."

"Good," she said, and got off him for a second. She opened the drawer to her coffee table and pulled out what Regulus realized was a condom, then pushed it into his hand. "Here, put this on."

Okay…Regulus knew what these were, but he'd never worn one. Well, he could probably figure it out. He tore it open and slipped it on, like a hand in a glove. Meanwhile, Holly was taking off her jeans. They were very tight, so she had to kind of shimmy out of them, but they eventually dropped to her ankles, and she stepped out of them. Then she dropped her lacy black panties.

The closest Regulus had ever come to seeing a naked woman was when he "borrowed" the lady magazines Sirius bought at the Muggle drugstores when the boys were in their teens (and Regulus did more than just look at those pictures, too). There was nothing quite like a 1975 _Playboy_ photo spread to help a horny young man get off—nothing, that is, except the real thing.

Regulus got up off the couch, a little wobbly, hard enough to penetrate sheet metal at this point, but he knew he wasn't just supposed to throw her down on the couch and enter her just like that. He had to do something special first, something special for her. He wasn't really one to watch porn; he didn't really get turned on by it that much, because he knew the girls weren't really enjoying it. The best part was to know that a woman was feeling so good because of what he was doing to her. Unfortunately, thanks to not watching porn, he didn't really know what he was supposed to do. Besides knowing his penis had to get into her vagina somehow, he was quite lost.

 _Well, maybe I should just do what comes naturally_ , he thought to himself as he approached her, and that of course was play with her breasts. He could touch those all night long. As he cupped them in his hands, running his thumbs over the nipples, she shuddered pleasurably and whispered, "Bite them."

"What?" he said, hating how vulnerable his voice sounded.

"I said, bite them," Holly repeated. Getting your breasts sucked and licked might very well be the female version of a blow job, being such an erogenous zone, but Regulus knew he never would want to get bitten down there. That was painful to even think about. If these were sensitive parts of her, he didn't know why she would want them bitten, but maybe she was horny enough that a little pain would feel good.

"O-Okay," he stammered. Something told him not to bite too hard; just enough so that she could feel his teeth. He got the hang of it quickly, moving them around a little while she moaned and grabbed bunches of his hair. When he finished, straightening up, she grinned at him.

"I always love that, Reggie," she told him softly. "You know why? Because I get a wave of warmth down there, like someone lit a fire in my vagina. I can feel the wetness, too."

This was the sexiest thing Regulus had ever heard in his whole entire life, and that was not hyperbole. He grabbed her by the shoulders and kissed her passionately, loving her shriek of surprise. With each beat of his heart in his chest, he felt a throb in his penis. Hopefully he'd be inside her for more than five seconds before he exploded like a champagne bottle. Already his testicles were burning, very full and tingling with anticipation. It was all in anticipation, in fact, and he could barely stand it. As they kissed she ran her hand down his sides and slapped his rear end, giggling at his gasp.

"You want to feel just how wet, honey?" she asked, gesturing between her legs. "Those fingers are talented."

Regulus was feeling nervous, but after what she had done to him—what she had done _for_ him—how could he not? So he reached down, his hand shaking a little, and inserted one finger into her, then two.

"Not up _there_ ," said Holly. "That's where the pee comes from, Reg. Down _here_."

Regulus felt himself blushing again, but she seemed utterly shameless as she took his hand in hers and guided it downwards. He should have known this was the vagina; it was bigger, deeper, and soaking wet. That was hot. It was kind of embarrassing that she had to give him directions, but how else would he learn? Fingers, he knew, were not the same as a penis, just like a mouth wasn't a vagina, but maybe she liked the fact that he had more dexterity. He moved them around until he found a small, round part…when he hit that, she cried out and grabbed his hair again, breathing quickly, so he kept playing with it until he finally pulled his fingers out. They smelled a little funny, but he was too horny to really care that much.

"Down!" Holly almost shouted, reaching her arms up to Regulus's shoulders and he felt himself falling backwards onto the couch as she pushed him and held him there. She grabbed his Slytherin tie, which was lying on the floor, and bound his hands. Not so much that he couldn't break free if there was some kind of emergency, but enough that he couldn't really move his wrists. He felt a sudden spike in his libido as she straddled him.

"Oh, God!" Regulus cried as she grabbed his penis in both hands and positively shoved it into her vagina. It was even better than the blow job; he could feel every single nerve on his penis firing up as she flexed her vaginal muscles, making herself even tighter.

"Too rough?" she whispered in his ear.

"No!" Regulus moaned. "Keep going…please…"

"I can't hear you," she said.

"PLEASE!" he hollered, trying to move his hands, then remembering he couldn't.

Holly yanked his black hair with one hand and set the other one flat on the couch, and he could barely control his heavy breathing as she moved her big hips back and forth, up and down, all around. He could hear her own cries, the loudest one as her own warm, wet orgasm broke over her like a crashing wave on the beach, his penis hitting all different areas inside of her as she continued to grind him.

It was very, very, very good—the feeling of the friction as he moved in and out of her, his penis rubbing against her tight vaginal walls. He felt like he _belonged_ there, somehow. It seemed like with female orgasms, once a woman had one, it was sometimes easier for her to have another. That was probably what was going on with Holly, because now she wouldn't stop moaning.

"Faster!" said Regulus, and Holly obliged; he began feeling the muscles in his penis contract, and he knew then that this orgasm was on its way and he was completely powerless to stop it—not that he wanted to, of course. He recognized the sensation of his release inside him, leading up towards the tip of his penis (it always felt sort of like he needed to pee, times one thousand). Just a few seconds more and—

It was never as good as this, _never_ as good—he was grabbing her hair, groaning extremely loudly—all tension in his body was gone—pulses of semen collected in the condom as he finished himself off, another jolt of pleasure with each one…he just rode the wave of complete ecstasy, just letting it out…

And then it was over. Holly was getting off of him, laughing good-naturedly, untying his hands for him, but he could hardly feel it. His head collapsed back onto the couch as fatigue flooded him. He was exhausted, but happy. So happy. Nothing was wrong with the world.

"Do you need a drink, Reggie?" said Holly, using her wand to Summon her fluffy bathrobe and slipping it on. "You're dehydrated, aren't you?"

Regulus nodded, and she went to get him some water. She kneeled beside the couch and stroked his hair as he drank it, then she got a blanket and spread it over him when he was finally able to sit up. Next thing you know he was flushing the condom down the toilet, getting dressed again, and kissing her goodbye.

This was an evening he would not soon forget.


End file.
